allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Base Information

• Chemical Name: allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
• CAS No.: 113599-78-3
• Molecular Formula: C₃₀H₂₇ClN₂O₄
• Molecular Weight: 515.008

Synonyms:allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Chemical Property of allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

There total 7 articles about allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

allyl 2-<(3S,4S)-4-(hydroxymethyl)-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-4-chlorobutanoate (113599-71-6) → allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-78-3)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 0.25h;

DOI:10.1021/jm00401a020

Reference yield:

allyl bromoacetate (40630-84-0) → allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-78-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent

2: LiN(SiMe₃)2 / tetrahydrofuran / -78 °C

3: tetrabutylammonium fluoride, HOAc / tetrahydrofuran

4: di-isopropyl azodicarboxylate, triphenylphosphine / tetrahydrofuran

With di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1039/c39870001283

Reference yield:

(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-3-(tritylamino)-2-azetidinone (113599-61-4) → allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate (113599-78-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent

2: LiN(SiMe₃)2 / tetrahydrofuran / -78 °C

3: tetrabutylammonium fluoride, HOAc / tetrahydrofuran

4: di-isopropyl azodicarboxylate, triphenylphosphine / tetrahydrofuran

With di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1039/c39870001283

upstream raw materials:

allyl 2-<(3S,4S)-4-(hydroxymethyl)-2-oxo-3-tritylamino-1-azetidinyl>-3-oxo-4-chlorobutanoate

allyl bromoacetate

(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-3-(tritylamino)-2-azetidinone

allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-(tritylamino)-1-azetidinyl>acetate

Downstream raw materials:

allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-(chloromethyl)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate

(6S,7S)-7-[(R)-2-Allyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-3-iodomethyl-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid allyl ester

{(6S,7S)-2-Allyloxycarbonyl-7-[(R)-2-allyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-8-oxo-4-oxa-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl}-triphenyl-phosphonium; iodide

(6S,7S)-7-<<(R)-2-(4-hydroxyphenyl)glycyl>amino>-8-oxo-3-(cis-1-propenyl)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylic acid

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